A New Synthesis of Sulfur-, Nitrogen- and Oxygen-Containing Eight-Membered Ring Lactams

作者：Pflantz Rebekka; Sluiter Jonas; Kricka Mario; Saak Wolfgang; Hoenke Christoph; Christoffers Jens^*

来源：European Journal of Organic Chemistry, 2009, 2009(31): 5431-5436.

DOI：10.1002/ejoc.200900825

• Lactams
• Heterocycles
• Sulfur compounds
• Medium ring compounds
• Ring expansion
• Amines

Bi(NO(3))(3)-catalyzed ring expansion of five-membered ring 1,4-diketones in the presence of primary amines leads to eight-membered ring lactams. When applied to starting materials with a tetrahydrothiophene or pyrrolidine moiety, tetrahydro-2H-1,4-thiazocin-3-ones and hexahydro-1,4-diazocin-2-ones are obtained as representatives of these very rare heterocyclic systems. In the case of tetrahydrofuran derivatives, other reaction conditions are required and yields of tetrahydro-2H-1,4-oxazocin-3-ones are very low.

• 出版日期2009-11